Songs About Dating in Your 20s

Dating in My 20s: A Retrospective Playlist

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We've all been through it. You go on a great first date full of real smiles and honest laughs only to feel befuddled and deflated five days later when they haven't called to schedule another. Or maybe you didn't call, because even though they're's perfect on paper, your first thought on returning home wasn't about a second date, but whether to use a crockpot or the stovetop to make soup for tomorrow's dinner.

I recently realized that dating is just weird. Sometimes it's great and sometimes it's awful, but it's always weird. And what better way to illustrate the weirdness than with a playlist? These songs tell the story much better than I ever could. Some are inspired by specific memories, but most are dedicated to the archetypal experiences themselves (who hasn't dated a literal or metaphorical cowboy at least once in their 20s?).

1. The One Who Was Almost "The One"

For a while, you thought this was it. But then, for a million small reasons or maybe just one big one, the relationship ended, you parted ways, and even if it was for the best, it almost killed you.

2. That Person You Met on Vacation

Song: "Cool For the Summer" by Demi Lovato

So you go on vacation and meet an Australian kite salesperson at the pool. You don't know their middle name and you're unclear on what they actually do for a living, but you are suddenly very curious about what your children might look like. How much money is in your savings account — could you quit your job? What kind of visa do you need to move to Australia? Is that crazy? (Yes.)

3. Falling in Love With Your Best Friend

Song: "Stella" by Cereus Bright

Well, that was clearly insane. You come home and settle back in, calling your best friend to tell them all the details. But wait, didn't you miss them more than you expected to while you were away? They're probably the only person who has seen you without makeup or crying over penguins at the zoo, and the one who hangs out with you anyway. Remember that time they pretended to propose to you in front of that group of Japanese tourists? When you think about it, they've been there all along. Why didn't you think of this before?

4. Realizing It Was Probably a Bad Idea to Date Your Best Friend

5. That Time You Dated a Cowboy

Song: "Cruise" by Florida Georgia Line

So you nurse your doubly broken heart with someone totally different in every conceivable way. It is in no way built to last, but hey, here's to drinking a little more Lone Star and stepping a little further outside your comfort zone.

6. After a Really, Really Good First Date (Especially After a Lot of Really, Really Bad Ones)

Then you meet a new guy at a kickball tournament and you flirt for a while before you meet up for drinks on a Saturday night. After three drinks, he walks you home, and BAM! There it is. Is there anything more thrilling than your first kiss after a truly good first date? One filled with so much anticipation that you can feel your body literally melt into the other person? You can feel every hair on your body standing on end. Hey — maybe this is it?

7. Trying to Remember Why You Started Dating Them in the First Place

Song: "Crooked Teeth" by Death Cab For Cutie

No, this is definitely not it. What did you like about this one again?

8. Breaking Up

Pretty sure these songs speak for themselves. Either way, you're crying and you've sworn off an entire portion of the city because that's where they get their coffee. Note: in only one case are you metaphorically holding a pair of rusty kitchen scissors.

9. When They "Just Can't Decide What They Want"

Song: "TTYN" by Vivienxo

So they show up at your door (or more realistically, on your phone) to tell you that they love you and want a second chance. Or . . . maybe they love you and want a second chance? They're not sure, but they want you to know that they think you're so special. They're totally not in love with their roommate anymore. Can they just have some time? (No.)

10. When You Just Can't Decide What You Want

Song: "How to Be a Heartbreaker" by Marina and the Diamonds

Now they're back, but you're not so sure. Why did it take them so long to figure it out? Do they just want you because now you're seeing someone else? Does any of this even matter because you're definitely still planning to spend a year in London before you settle down. Can you trust them? This all feels very, very complicated. Surely you are the first person in history to have this dilemma.

11. Getting Back Together

Song: "Want U Back" by Cher Lloyd

Your friends are maximum skeptical. They're doing that thing where they speak very slowly and deliberately, telling you with their mouths that they trust your judgment and with their eyes that you're an idiot.

But feelings don't just go away. You had something really special and besides, dating is the worst. You don't want to have any regrets. You'll give it one more chance.

12. Breaking Up Again

13. Getting Your Groove Back

Song: "Return of the Mack" by Mark Morrison (Alternately: "Missin' You" by The Summer Set)

In a slump for weeks, you wake up one morning to find that the sun is shining and something feels different. You look around — nothing is out of place. You're not late for work; the dishes are done. So what's different? Could it — could it be? Could it be that you're . . . happy?

Damn straight. Because you've finally realized that it never mattered what he thought about you. You like you, and you spend far more time with yourself than he ever could. You may find someone to share your life with, but if and when that day comes, it will be because you want someone, not because you need them to validate who you are or why you matter.

You walk out your front door into the sunshine. The day stretches out in front of you, yours for the taking.

14. Realizing It's All a Beautiful Mess

So, again, dating is weird. Who wants to get all dressed up, put their life on display for a complete stranger, and then sit there waiting to be rejected? Sociopaths, that's who.

But here's the thing: dating is also kind of amazing. The whole purpose is to get out into the world, try new things, and meet new people — if you're not a little bit uncomfortable, I think you might be doing it wrong. Even the worst dates teach you something — about yourself, about what you like, about what you hate more than literally anything on this planet, about the life you're building for yourself.

Did this playlist seem a little manic to you? Good, because living it was, too. Wouldn't change anything, though. So, regardless of all the ups, downs, tears, and fears, I'm feeling pretty good about the last seven years. And I've still got two left!

Plus, as Fletcher reminds us, "Maybe it's a good thing to go through a little hell."